FR2329275A1 - Sedative phenyl-alkyl-triazoles - which may be prepd. by decarboxylation of a carboxylated triazole - Google Patents

Sedative phenyl-alkyl-triazoles - which may be prepd. by decarboxylation of a carboxylated triazole

Info

Publication number
FR2329275A1
FR2329275A1 FR7632136A FR7632136A FR2329275A1 FR 2329275 A1 FR2329275 A1 FR 2329275A1 FR 7632136 A FR7632136 A FR 7632136A FR 7632136 A FR7632136 A FR 7632136A FR 2329275 A1 FR2329275 A1 FR 2329275A1
Authority
FR
France
Prior art keywords
alkyl
phenyl
substd
ring
halogens
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7632136A
Other languages
French (fr)
Other versions
FR2329275B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zeneca Inc
Original Assignee
ICI Americas Inc
ICI United States Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ICI Americas Inc, ICI United States Inc filed Critical ICI Americas Inc
Publication of FR2329275A1 publication Critical patent/FR2329275A1/en
Application granted granted Critical
Publication of FR2329275B1 publication Critical patent/FR2329275B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles

Abstract

Novel substd. triazoles are of formula (I) (where R1 and R2 are H, carboxy, phenyl, 1-4C alkyl, amino, 1-piperidinecarbonyl 1-4C hydroxyalkyl, or together are 1,3-butadienylene forming a benzoid ring; one of R3 and R4, in combination with the dotted circle, is two double bonds; with the proviso that (a) when R1 and R2 are H, R3 is opt. substd. aliphatic, aromatic or heterocyclic gp., e.g. 4-6C alkyl, 8-12C phenyl alkyl or 9-14C 3-indole alkyl; (b) when R1 and R2 are H, R4 is 7-12C phenyl alkyl (opt. substd. by o-halogen, m-Cl, p-Br, 2-3 halogens on the ring, mono-di or trihalo alkyl on the ring or 1-3 alkyl on the ring), 6-9C pyridylalkyl, or 8-13C benzoylalkyl (substd. by 1-3 halogens on the ring); (c) when one of R1 and R2 is H and the other is not H, R3 is hexyl, 8-12C phenyl branched alkyl, 7-12C phenylalkyl (substd. on the ring by 1-3 halogens) or 7-10C phenylalkyl (substd. on the ring by 1-3, 1-4C haloalkyl and 1-5 halogens); and (d) when R1 and R2 are butadienylene, one of R3 and R4 is 8-10c phenyl alkyl or 7-10C phenyl alkyl substd. by 2-4 halogen). A typical cpd. is 1-(3-phenylpropyl)-1H-1,2,3-triazolo, prepd. by decarboxylation (200-225 degrees C) of the corresp. 4,5-dicarboxy cpd.
FR7632136A 1975-10-28 1976-10-25 Sedative phenyl-alkyl-triazoles - which may be prepd. by decarboxylation of a carboxylated triazole Granted FR2329275A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US62614075A 1975-10-28 1975-10-28

Publications (2)

Publication Number Publication Date
FR2329275A1 true FR2329275A1 (en) 1977-05-27
FR2329275B1 FR2329275B1 (en) 1978-12-15

Family

ID=24509116

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7632136A Granted FR2329275A1 (en) 1975-10-28 1976-10-25 Sedative phenyl-alkyl-triazoles - which may be prepd. by decarboxylation of a carboxylated triazole

Country Status (12)

Country Link
JP (1) JPS5253863A (en)
AU (1) AU1881176A (en)
BE (1) BE847480A (en)
DE (1) DE2648826A1 (en)
DK (1) DK478176A (en)
FI (1) FI763050A (en)
FR (1) FR2329275A1 (en)
IL (1) IL50699A0 (en)
LU (1) LU76062A1 (en)
NL (1) NL7611944A (en)
NO (1) NO763569L (en)
SE (1) SE7611884L (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005000821A1 (en) * 2003-06-12 2005-01-06 Eli Lilly And Company Tachykinin receptor antagonists
US7179804B2 (en) 2002-04-26 2007-02-20 Eli Lilly And Company Tachykinin receptor antagonists
US7320994B2 (en) 2002-04-26 2008-01-22 Eli Lilly And Company Triazole derivatives as tachykinin receptor antagonists
US9060995B2 (en) 2012-01-26 2015-06-23 Vanda Pharmaceuticals, Inc. Treatment of circadian rhythm disorders
US9730910B2 (en) 2012-12-18 2017-08-15 Vanda Pharmaceuticals, Inc. Treatment of circadian rhythm disorders
US11090285B2 (en) 2013-11-12 2021-08-17 Vanda Pharmaceuticals Inc Treatment of circadian rhythm disorders
US11786502B2 (en) 2013-11-12 2023-10-17 Vanda Pharmaceuticals Inc. Method of treatment
US11918557B2 (en) 2012-01-26 2024-03-05 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI834666A (en) * 1982-12-23 1984-06-24 Ciba Geigy Ag FOERFARANDE FOER FRAMSTAELLNING AV NYA ARALKYLTRIAZOLFOERENINGAR.
US4801594A (en) * 1984-06-18 1989-01-31 Eli Lilly And Company Aromatase inhibitors
CA2015267A1 (en) * 1989-05-26 1990-11-26 Rainer Seele 8-azolylmethylquinolines
LT3250563T (en) 2015-01-30 2022-04-11 Neurocrine Biosciences, Inc. Substituted triazoles and methods relating thereto
US9771335B2 (en) * 2015-07-31 2017-09-26 The Johns Hopkins University Derivatives of rufinamide and their use in inhibtion of the activation of human voltage-gated sodium channels
CN105801499A (en) * 2016-04-15 2016-07-27 华东理工大学 Design of preparing novel OLED reagent from ketene and application thereof
CN111196785B (en) * 2020-01-21 2021-08-31 成都新朝阳作物科学股份有限公司 Triazole derivative and preparation method and application thereof

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7179804B2 (en) 2002-04-26 2007-02-20 Eli Lilly And Company Tachykinin receptor antagonists
US7320994B2 (en) 2002-04-26 2008-01-22 Eli Lilly And Company Triazole derivatives as tachykinin receptor antagonists
WO2005000821A1 (en) * 2003-06-12 2005-01-06 Eli Lilly And Company Tachykinin receptor antagonists
US10610510B2 (en) 2012-01-26 2020-04-07 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US11826339B2 (en) 2012-01-26 2023-11-28 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US9549913B2 (en) 2012-01-26 2017-01-24 Vanda Pharmaceuticals, Inc. Treatment of circadian rhythm disorders
US11918556B2 (en) 2012-01-26 2024-03-05 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US9855241B2 (en) 2012-01-26 2018-01-02 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US10149829B2 (en) 2012-01-26 2018-12-11 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US10449176B2 (en) 2012-01-26 2019-10-22 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US9060995B2 (en) 2012-01-26 2015-06-23 Vanda Pharmaceuticals, Inc. Treatment of circadian rhythm disorders
US10945988B2 (en) 2012-01-26 2021-03-16 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US11918557B2 (en) 2012-01-26 2024-03-05 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US11285129B2 (en) 2012-01-26 2022-03-29 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US11633377B2 (en) 2012-01-26 2023-04-25 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US11850229B2 (en) 2012-01-26 2023-12-26 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US9539234B2 (en) 2012-01-26 2017-01-10 Vanda Pharmaceuticals, Inc. Treatment of circadian rhythm disorders
US11833130B2 (en) 2012-01-26 2023-12-05 Vanda Pharmaceuticals Inc. Treatment of circadian rhythm disorders
US9730910B2 (en) 2012-12-18 2017-08-15 Vanda Pharmaceuticals, Inc. Treatment of circadian rhythm disorders
US11786502B2 (en) 2013-11-12 2023-10-17 Vanda Pharmaceuticals Inc. Method of treatment
US11090285B2 (en) 2013-11-12 2021-08-17 Vanda Pharmaceuticals Inc Treatment of circadian rhythm disorders

Also Published As

Publication number Publication date
LU76062A1 (en) 1977-05-18
IL50699A0 (en) 1976-12-31
FR2329275B1 (en) 1978-12-15
DK478176A (en) 1977-04-29
NO763569L (en) 1977-04-29
AU1881176A (en) 1978-04-27
DE2648826A1 (en) 1977-05-05
JPS5253863A (en) 1977-04-30
NL7611944A (en) 1977-05-02
SE7611884L (en) 1977-04-29
FI763050A (en) 1977-04-29
BE847480A (en) 1977-04-20

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Legal Events

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